Patent GB-589232-A (GB)
Title: Manufacture of new betaine derivatives
IPC: C07J75/00
Filed: 1944-02-23
Abstract: Esters of betaine salts are obtained by treating a hydroxy compound, of the steroid or other alicyclic series or of the aliphatic open chain series or of the aryl series, with an acid halide or anhydride of a salt of betaine.  It is advantageous to treat a mixture of such a hydroxy compound and a compound which does not react with the betaine component to separate the resulting ester in known manner and to regenerate the hydroxy compound by saponification.  Specified hydroxy compounds are: octadecyl alcohol, alicyclic alcohols, e.g. menthol and vitamin A, and alcohols of the steroid series such as tertosterone, androsterone, corticosterone, desoxycorticosterone, dehydrocorticosterone, oestrone, oestradiol or a mono-ester thereof, and also genins of synthetic or natural cardio-active substances and glycosides thereof such as strophanthidin, strophanthin, digitoxigenin, gitoxin, gitoxizenin; and aryl hydroxy compounds, e.g. phenols, cresols, chlorophenols and 2-methyl-naphtho hydroquinone. The acid halides or anhydrides of salts of betaine may be obtained from betaine or salts or ester-salts thereof by the action of suitable agents.  The reaction medium is advantageously an inert solvent and/or an acid binding agent, e.g. pyridine or other tertiary bases.  In examples there are prepared betaine chloride esters of: (1) cholesterol, by boiling a chloroform solution of cholesterol and the acid chloride of betaine chloride (prepared from betaine chloride and phosphorus pentachloride dissolved in acetyl chloride and by the method of, the corresponding esters of (2) cholestanol; (3) strophanthidine; (4) D 5 : 6 ; 20 : 22-3 : 21-dioxy-non-choladienic acid lactone; (5) menthol; (6) octadecyl alcohol; (7) para-oxybenzoic acid methyl ester; (8) pregnanediol residue (prepared from urine of pregnancy by treatment with the chloride of trimethylammonium acetic acid anhydride; (9) androstene dione, after biochemical reduction in known manner; (10) b 1-[D 5 - 3b  - oxy - nor - cholenyl-(23)]-D a 1 : b 1-butenolid.  The process may also be used for converting substances insoluble in water into water-soluble substances, e.g. dyestuffs, pharmacological and physiologically active compounds such as aglucones.  Sparingly water-soluble salts of the betaine esters are also specified, viz. the picrate, chloroplatinate, double salt with mercury (which may be reconverted to the ester by the action of hydrogen sulphide), the preparation of which are described; and other specified salts are: the chloroaurate, reineckate and picronolate. The salts with many acids and alkaloid reagents are also specified. In the Specification as open to inspection under Sect. 91, the invention therein defined discloses that any organic compound containing a reactive hydrogen atom or metal atom capable of being exchanged for an acyl group may be used as component to react with the betaine component.  Other specified starting materials are accordingly included, viz. vitamin E, primary and secondary amines or corresponding alkaloids; b -diketones, b -ketocarboxylic acid derivatives and the corresponding metal compounds of the aforesaid substances.  This subject-matter does not appear in the Specification as accepted.